Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC))vol.14

524 Pages·1983·3.24 MB·English

by  J. H. Jones

Am i no -acids, Pe pt ides,
and Proteins
Volume 14
A Specialist Periodical Report
Amino-acids, Peptides, and
Proteins
Volume 14
A Review of the Literature Published
during 1981
Senior Reporter
J H Jones University of Oxford
Reporters
0 Adams University of Newcastle upon Tyne
T Atkinson PHLS Centre for Applied Microbiology and Research, Porton Down,
Wiltshire
G C Barrett Oxford Polytechnic
D Brandenburg Deutsches Wollforschungsinstitut, Aachen, West Germany
T Brittain University of Auckland, Auckland, New Zealand
R Cassels Beecham Pharmaceuticals, Epsom, Surrey
D L Christie University of Oxford
D H Coy Tulane University of Louisiana, New Orleans, Louisiana, USA
R Devonshire University of Sheffield
D P E Dickson University of Liverpool
A Electricwala PHLS Centre for Applied Microbiology and Research, Porton Down,
Wiltshire
J Gagnon University of Oxford
I J Galpin University of Liverpool
P M Harnrnond PHLS Centre for Applied Microbiology and Research, Porton Down,
Wiltshire
G W Hardy Wellcome Research Laboratories, Beckenham, Kent
P M Hardy University of Exeter
P D Jeffrey Australian National University, Canberra, Australia
(continued overleaf)
The Royal Society of Chemistry
Burlington House, London W1 V OBN
ISBN 0-85186-124-5
ISSN 0306-0004
Copyright @ 1983
The Royal Society of Chemistry
All Righrs Roserved
NO part Of'tliisb ook m~iyhe reprodwed or transmitted in unj<,formo r by uny meuns-graphic,
electronic, including photocopying, recording, tuping, or injormation storuge and retrieid
.sj,steni.s~i~,ithowutr itten permission ,from The Royul Society of' Chemistry
Reporters (continued)
M Manning Medical College of Ohio, Toledo, Ohio, USA
W D Mercer Queen's University of Belfast
L W N ichol Australian National University, Canberra, Australia
A Olma Technical University, Lodz, Poland
R H Pain University of Newcastle upon Tyne
J Ramachandran University of California, San Francisco, California, USA
H W E Rattle Portsmouth Polytechnic
N K Rogers University of Oxford
P D Roy Oce-Andeno B.V., Venlo, The Netherlands
D Saunders Deutsches Wollforschungsinstitut, Aachen, West Germany
W H Sawyer Columbia University, New York, USA
M D Scawen PHLS Centre for Applied Microbiology and Research, Porton Down,
Wiltshire
A Schuttler Deutsches Wollforschungsinstitut, Aachen, West Germany
R J Sherwood PHLS Centre for Applied Microbiology and Research, Porton Down,
Wiltshire
R A G Smith Beecham Pharmaceuticals, Epsom, Surrey
R M Stephens Portsmouth Polytechnic
M J E Sternberg University of Oxford
D J Win zor University of Queensland, Queensland, Australia
Typeset and printed in Great Britain by John Wright & Sons (Printing) Ltd. at The Stonebridge Press,
Bristol
Preface
This fourteenth Report reviews papers that are relevant to the chemistry of amino-
acids, peptides, and proteins published during 1981, except in the contribution on
Primary Structures, where the coverage is for 1980 and 1981 (making good a
regretted omission from the thirteenth Report).
The format and style of the Report are very much as established by previous
volumes, but in some sections the pressures of time and space have been met by
cutting discussion even more drastically than before and presenting almost all the
information in an easily scanned tabular form. Also, it is now the Society’s policy
to dispense with indexes in Specialist Periodical Reports except in special cases.
This Report conforms with that policy by dropping the Author Index, which has
been regular hitherto, as a contribution towards the minimization of production
costs and delay. The coverage in Chapter 5, which deals with Structure and
Biological ,Activity, is, as sometimes before, not quite comprehensive: the
Gastrointestinal Hormones and Thyroid and Parathyroid Hormones are notable
lacunae. It is hoped to remedy these gaps if this chapter remains a standard feature
of the Reports.
The changeover in the Senior Reportership occasioned a little delay in making
the necessary arrangements, and the contributors had to work under some
pressure. I am grateful to them for accepting their tasks at rather short notice - in
several cases in spite of other demanding commitments and for their patience in
-
the face of my harassment.
Bob Sheppard’s run as Senior Reporter has been a long (Volumes 5-13) and
distinguished one: I am very grateful to him for his efforts to make the changeover
smooth and for much valuable advice. He was only the second Senior Reporter in
the series: the first was Geoffrey Young (Volumes 1-4), who established the basic
essentials of the structure to which the Reports still adhere. Geoffrey retires this
year from Oxford, where he has been a Fellow of Jesus College since 1947 (Vice-
Principal 1969-1 972, Acting Principal 1973-1977), University Lecturer in
Organic Chemistry 1952-70, and Aldrichian Praelector in Chemistry since 1970.
He was trained in carbohydrate chemistry at Bristol under E. L. Hirst but, after
wartime work in explosives research, he turned to amino-acids and peptides. These
have retained his interest ever since. His principal numbered series of full papers,
which has almost made its half century, records a succession of important
contributions to the art of peptide synthesis especially on the racemization
-
problem, on protective groups, and on the application of basic ‘handles’ to
facilitate isolation and purification. A correspondent of Josef Rudinger from
about 1949, he was one of the pioneering handful who were invited by him to the
first of the European Peptide Symposia (Prague, 1958) and has been very
prominent in the regular series thus initiated. Nearer home, he was the leading
figure in the foundation of the Chemical Society Peptide and Protein Group and
was its first Secretary 1968-1969 and later Chairman 1972-1975. He has earned
the affection of his pupils and the respect of everyone in the field; he steps down as
the doyen of British peptide chemistry.
Bulliol College, Oxfhrd JOHNJ ONES
September 1982
Contents
Chapter 1 Amino-acids
By G. C. Barrett
1 Introduction 1
Textbooks and Reviews 1
2 Naturally Occurring Amino-acids 1
Occurrence of Known Amino-acids 1
New Natural Amino-acids 3
New Amino-acids from Hydrolysates 4
3 Chemical Synthesis and Resolution of Amino-acids 5
General Methods of Synthesis of a-Amino-acids 5
General Methods of Synthesis of p- and Higher Hom-
ologous Amino-acids 6
Asymmetric Synthesis of Amino-acids 7
Prebiotic Synthesis; Model Reactions 8
Protein and Other Naturally Occurring Amino-acids 9
r-Alkyl Analogues of Protein Amino-acids 11
C-Alkyl and Substituted C-Alkyl Amino-acids 11
Aliphatic Amino-acids Carrying Halogen Substituents
in Side Chains 12
Aliphatic Amino-acids Carrying Hydroxy Groups in
Side Chains 12
Unsaturated r-Amino-acids 13
Synthesis of Amino-acids with Aromatic and Hetero-
aromatic Side Chains 14
r-H ydroxyamino-acids 14
Synthesis of ct-Amino-acids Containing Sulphur and
Selenium 14
Labelled Amino-acids 14
Resolution of Amino-acids 16
4 Physical and Stereochemical Studies of Amino-acids 17
Crystal Structures of Amino-acids and Their Derivatives 17
Nuclear Magnetic Resonance Spectrometry 18
Optical Rotatory Dispersion and Circular Dichroism 19
Mass Spectrometry 20
Other Physical Studies 21
Molecular-orbital Calculations 22
vii
...
Vlll Contents
5 Chemical Studies of Amino-acids 23
Racemization 23
Specific Reactions of Natural Amino-acids 23
General Reactions 26
Effects of Electromagnetic Radiation on Amino-acids 28
6 Analytical Methods 29
Gas-Liquid Chromatography 29
Ion-exchange Chromatography 30
Thin-layer Chromatography 30
High-performance Liquid Chromatography 31
Other Analytical Methods 32
Determination of Specific Amino-acids 32
Chapter 2 Structural Investigations of Peptides and
Proteins
lA: P ro tein /so la ti0n and Ch ar a c teriza ti0 n
By M. D. Scawen, R. J. Sherwood,
P. M. Hammond, A. Electricwala, and
T. A tkinson
1 Introduction 34
2 Protein Isolation Methodology 34
Affinity Chromatography 34
General Comments 34
Coupling Techniques 35
Affinity Elution 36
Dye-affinity Chromatography 36
Other Applications and Techniques 37
Hydrophobic Interaction Chromatography and Co-
valent Chromatography 37
Immunoaffinity Chromatography 51
Metal Chelate Chromatography 58
Phase Partition and Partition Chromatography 58
High-performance Liquid Chromatography 59
Other Chromatographic Techniques and Applications 60
3 Isolation of Specific Classes of Proteins 60
Membrane Proteins 60
Plasma Proteins 61
Proteins Involved with Coagulation and Fibrinolysis 61
Plasma Fibronectin 72
Complement and Associated Proteins 72
Other Plasma Proteins 72
Con tents ix
4 Protein Characterization 72
Protein Determination in Solution 72
Protein Detection in Gels 74
Electrophoretic Techniques 75
One-dimensional Electrophoresis 75
Isoelectric Focusing 78
Two-dimensional Electrophoresis 80
Immunoelectrophoresis 81
Affinity Electrophoresis 81
Isotachophoresis 82
Chromatofocusing 83
Molecular-weight Determination 84
IB: Primary Structures, 7980 and 7987
By J. Gagnon and D. L. Christie
1 Amino-acid Sequences Reported During 1980 85
Blood-clotting Proteins 85
Complement Proteins 85
Electron-transport Proteins 86
Enzymes 87
Globins 92
Histocompatibility Antigens and Antibodies 94
Histones 97
Hormones 98
Ribosomal Proteins 99
Structural Proteins 100
Toxins 101
Viral Proteins 101
Miscellaneous Peptides and Proteins 102
2 Amino-acid Sequences Reported During 1981 107
Blood-clotting Proteins 107
Complement Proteins 107
Electron-transport Proteins 108
Enzymes 109
Globins 114
Histocompatability Antigens and Antibodies 115
His tones 118
Hormones 118
Ribosomal Proteins 121
Structural Proteins 122
Toxins 122
Viral Proteins 123
Miscellaneous Peptides and Proteins 12 4
Con tents
X
IC: Chemical Modification of Proteins
By R. Cassels and R. A. G. Smith
1 Introduction i32
2 Investigations of Known and Novel Reagents and Reactions 89
Butane-2,3-dione 89
Diethyl Pyrocarbonate 89
Iodoacetate and Iodoacetamide 89
o- Iodosob enzoic Acid 89
Methyl Acetimidate 89
N-( 3-Pyreny1)maleimide 190
Tetranitromethane 190
Triazine Dyes 190
Crosslinking Reagents 190
Fluorescent Reagents 193
Mechanism-based Inhibitors 194
Affinity Labelling 195
11: X-Ray Studies
By W. 0. Mercer
1 Introduction 198
2 Methods and Equipment 198
General Crystallographic Theory 198
Direct Methods 199
Data-collection Methods and Equipment 199
Crystal Growth 204
Protein Dynamics 204
Cryoenzymology 204
Protein-structure Determinations 205
3 Immunoglobulins 205
Human F, Fragment 20 5
4 Oxygen Carriers and Electron-transfer Proteins 206
Haem-protein Stereochemistry 206
Myoglobin 206
Haemoglobins 206
General 206
Human Haemoglobin 206
Horse Methaemoglobin 206
Mutant Haemoglobins 207
Crocodile Haemoglobin 207
Sickling Haemoglobin 207